Patent GB-661912-A (GB)
Title: Dyeing process and dyestuffs preparations therefor
IPC: D06P1/62
Filed: 1949-03-11
Abstract: Water-soluble aldehydes containing one of the following groupings <FORM:0661912/IV (b)/1> or <FORM:0661912/IV (b)/2> or <FORM:0661912/IV (b)/3> are prepared by treating two molecules of an amino-aldehyde containing a solubilizing group (or two molecules of different amino-compounds containing together at least one aldehyde and one solubilizing group) with phosgene, 2 : 4-dichlorquinazoline or cyanuric chloride.  In the last-named case, the third chlorine atom may be exchanged for a hydroxyl group or reacted with ammonia or an amine (e.g. aniline).  The groupings shown above are preferably attached to aromatic nuclei, and the aldehyde and solubilizing groups may be attached to the same or different nuclei.  There may be more than one aldehyde and/or solubilizing group present.  In the examples: (1) sodium sulphanilate is reacted with cyanuric chloride and the product treated successively with 3-aminobenzaldehyde and ammonia; the sulphanilate may be replaced by metanilate or naphthionate; (2) benzidine-2 : 21-disulphonic acid is reacted with 2 mols. of cyanuric chloride and the product treated successively with 3-amino-benzaldehyde and ammonia; the benzidinedisulphonic acid may be replaced by 4 : 41-diamino-stilbene-2 : 21-disulphonic acid; (3) 3-amino-benzaldehyde-6-sulphonic acid is reacted with cyanuric chloride and the product treated successively with 3-amino-benzaldehyde and ammonia; (4) phosgene is reacted with 2 mols. of sodium 4-amino-benzaldehyde-2-sulphonate.  Other specified reactants are ammonia, alkylamines such as butylamine, mono- and diethanolamine, aniline, benzidine, sulphonic acids of primary and secondary aliphatic amines such as taurine and N-methyl-taurine, orthanilic acid, aniline-disulphonic acids (e.g. 2 : 4-), naphthylamine-mono-, di- and tri-sulphonic acids (e.g. 1-naphthylamine-5-, 6-, 7-, 8-, 3 : 6-, 3 : 8- and 4 : 8-, and 2-naphthylamine-5-, 6-, 7-, 8-, 3 : 6- and 6 : 8-), diaminobenzenesulphonic acids (e.g. 1 : 3-diamino-4-sulphonic and 1 : 4-diamino-2-sulphonic), benzidine-mono- and di-sulphonic acids (e.g. 3-), sulphonic acids of amino-diaryl ethers (e.g. 2-amino-41-methyldiphenyl ether-4-sulphonic acid), aminoaldehydes such as 2- and 4-aminobenzaldehydes and 2-chloro-5-aminobenzaldehyde and aminoaldehyde-sulphonic acids such as 3-aminobenzaldehyde-4-sulphonic acid.  If the aldehydes are prepared in the form of free acids they may be converted into water-soluble salts, e.g. sodium salts.ALSO:Wool is dyed with complex chromium compounds of o-oxy-o1-amino-monoazo dyestuffs in the presence of a water-soluble aldehyde having affinity for wool.  The amino group in the dyestuffs may be primary or secondary, the dyestuffs being preferably derived from diazotized aminophenols (which may be substituted, e.g. with nitro groups) and naphthylamines or derivatives thereof, at least one sulphonic acid group being present. The aldehyde itself may or may not be a dyestuff and preferably contains a carboxylic or sulphonic acid group.  It should be adsorbed by the fibre to an extent of at least 60 per cent under stated conditions.  Colourless aldehydes that are suitable are those obtained by coupling two molecules of (preferably aromatic) amino-compounds with phosgene, 2 : 4 - dichloro - quinazoline or cyanuric chloride, there being one or more aldehyde and solubilizing groups in the product.  In the case of cyanuric chloride, the third chlorine atom is subsequently replaced by a hydroxyl, amino or substituted amino group.  A list is given of suitable amino-compounds from which the aldehydes may be prepared (see Group IV (b)).  When coloured aldehydes are used, they are preferably yellow (e.g. arylazo-pyrazolones), to prevent any undesirable effect on the shade of the chrome dyeing. Suitable pyrazolones are mentioned, including those described in Specification 205,503, [Class 2 (iii)]. Advantageously, a colourless aldehyde is used together with an aldehyde dyestuff. The dyeing is carried out in the usual way, e.g. in the presence of sulphuric acid and sodium sulphate.  Examples are given of dyeings carried out with both coloured and colourless aldehydes and with mixtures of the two.  Specification 654,023 and U.S.A. Specification 2,422,586 also are referred to.  Dyestuff preparations may be made by mixing together salts of the chromiferous dyestuff and salts of the aldehydes (coloured, colourless or mixed). Alternatively, the free acids may be mixed, jointly neutralized and dried.  Such preparations may also contain other salts (e.g. sodium chloride or sulphate) and/or dispersing agents.  Examples are given of suitable preparations.  Aldehydo-dyestuffs, i.e. water-soluble dyestuffs containing one or more aldehyde groups, are prepared by usual methods, the following being specified: 3-aminobenzaldehyde --> 1 - (21 : 51 - dichloro - 41 - sulpho - phenyl) - 3 - methyl - 5 - pyrazolone, 3 - aminobenzaldehyde --> 1 - (41 - sulpho - phenyl) - 5 - pyrazolone-3-carboxylic acid, 3-aminobenzaldehyde --> 1-(41 - sulpho - 11 - naphthyl) - 3 - methyl - 5 - pyrazolone, 3 - aminobenzaldehyde --> 1 - (21 - chloro - 51 - sulpho - phenyl) - 3 - methyl - pyrazolone, 3 - aminobenzaldehyde --> 1 - (21 - chloro - 51 - sulpho - phenyl) - 5 - pyrazolone - 3 - carboxylic acid and 3-aminobenzaldehyde --> 1 - (21-methyl-41-sulpho-phenyl)-3-methyl-5-pyrazolone.